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Synthesis
DOI: 10.1055/a-2088-4302
special topic

Selective Deuteration of Heterocycle N-Oxides via Iridium-catalyzed Hydrogen Isotope Exchange

Philippa Owens
1   Pure and Applied Chemistry, University of Strathclyde, Glasgow, United Kingdom of Great Britain and Northern Ireland
,
Blair Smith
1   Pure and Applied Chemistry, University of Strathclyde, Glasgow, United Kingdom of Great Britain and Northern Ireland
,
David Lindsay
1   Pure and Applied Chemistry, University of Strathclyde, Glasgow, United Kingdom of Great Britain and Northern Ireland
,
Sebastien Campos
2   Medicines Research Centre, GlaxoSmithKline Research & Development Limited, Stevenage, United Kingdom of Great Britain and Northern Ireland (Ringgold ID: RIN113460)
,
William J. Kerr 
3   Pure and Applied Chemistry, University of Strathclyde, Glasgow, United Kingdom of Great Britain and Northern Ireland
› Author AffiliationsSupported by: University of Strathclyde University Studentship
Supported by: Engineering and Physical Sciences Research Council EP/L505663/1
Supported by: GlaxoSmithKline EPSRC iCASE Studentship
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An iridium(I) N-heterocyclic carbene/phosphine complex has been applied to the C-H activation and hydrogen isotope exchange of quinoline N-oxides. The isotope labelling proceeds under exceptionally low catalyst loadings of 0.25 mol%, and delivers products with high levels of deuterium incorporation selectively at the C8 position. A broad substrate scope is demonstrated, with the method tolerant of electron-poor and -rich substrates, and of substitution adjacent to the site of C-H activation. The isotope label is fully retained under standard deoxygenation conditions to give the corresponding labelled quinoline, and the labelling and deoxygenation can be combined in a one-pot procedure.



Publication History

Received: 01 March 2023

Accepted after revision: 08 May 2023

Accepted Manuscript online:
08 May 2023

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